(2R,6R)-6-tert-butoxycarbonylaminomethyl-2-(5-tert-butyldimethylsilyloxypentanoyl)-4-methylmorpholine | 1099828-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (2R,6R)-6-tert-butoxycarbonylaminomethyl-2-(5-tert-butyldimethylsilyloxypentanoyl)-4-methylmorpholine
• CAS: 1099828-29-1
• 化学式: C₂₂H₄₄N₂O₅Si
• 分子量: 444.687
• InChiKey: CNEAVQREYSTIMW-IEBWSBKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  77.1
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,6R)-6-tert-butoxycarbonylaminomethyl-2-(5-tert-butyldimethylsilyloxypentanoyl)-4-methylmorpholine 在 四丁基氟化铵 、 四氯化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.5h， 以410 mg的产率得到(2R,6R)-6-tert-butoxycarbonylaminomethyl-2-(5-chloropentanoyl)-4-methylmorpholine
  参考文献：
  名称：

  A Flexible Route to Chiral 2-endo-Substituted 9-Oxabispidines and Their Application in the Enantioselective Oxidation of Secondary Alcohols

  摘要：

  A new and flexible route to enantiomerically pure bi- and tricyclic 9-oxabispidines has been developed with use of (1R,5S)-7-methyl-2-oxo-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester as the common late-stage intermediate. The 9-oxabispidines synthesized were evaluated as the chiral ligands in the Pd(II)-catalyzed oxidative kinetic resolution of secondary alcohols giving good to excellent selectivity factors of up to 19.

  DOI：

  10.1021/jo802409x
• 作为产物：
  描述：

  (1R,5S)-7-methyl-2-oxo-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester 、 (4-((tert-butyldimethylsilyl)oxy)butyl)magnesium bromide 以 四氢呋喃 为溶剂， 反应 1.5h， 以74%的产率得到(2R,6R)-6-tert-butoxycarbonylaminomethyl-2-(5-tert-butyldimethylsilyloxypentanoyl)-4-methylmorpholine
  参考文献：
  名称：

  A Flexible Route to Chiral 2-endo-Substituted 9-Oxabispidines and Their Application in the Enantioselective Oxidation of Secondary Alcohols

  摘要：

  A new and flexible route to enantiomerically pure bi- and tricyclic 9-oxabispidines has been developed with use of (1R,5S)-7-methyl-2-oxo-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester as the common late-stage intermediate. The 9-oxabispidines synthesized were evaluated as the chiral ligands in the Pd(II)-catalyzed oxidative kinetic resolution of secondary alcohols giving good to excellent selectivity factors of up to 19.

  DOI：

  10.1021/jo802409x